Annapolis Homes under $500,000

Annapolis Homes under $500,000

Welcome to Annapolis, Maryland—a city that beautifully marries rich history with vibrant coastal living. As the state capital and home to the United States Naval Academy, Annapolis offers a unique blend of cultural heritage and modern amenities. Nestled along the picturesque Chesapeake Bay, this charming city boasts a waterfront filled with sailboats, artisanal shops, and delightful eateries that cater to every palate.

For those looking to call Annapolis home without breaking the bank, you’ll be pleased to discover a selection of homes available for under $500,000. This makes Annapolis not just a dream destination but also an attainable one for first-time buyers, families, and those looking to invest in a thriving community. Whether you’re in the market for a cozy bungalow, a charming townhouse, or a quaint condo, there’s something here to suit every lifestyle.

Imagine waking up to the sound of seagulls and the gentle lapping of waves, all while being just a stone’s throw away from historic sites like the Maryland State House and the vibrant shops of Main Street. With excellent schools, beautiful parks, and a tight-knit community, Annapolis is more than just a place to live; it’s a place to thrive.

Discover your new home in Annapolis today, where history, community, and affordability come together in perfect harmony. Let us guide you through the exciting real estate options available in this enchanting city!

Newest Annapolis Homes under $500,000

no property photo
$269,000
3 Beds ⋅ 2 Baths
3 Bedroom 2 Bathroom spacious condo - COMING SOON!

21 Silverwood Cir Unit 3, Annapolis

Listing courtesy of Compass. Contact:

908 Windwhisper Ln, Annapolis
$499,000
3 Beds ⋅ 3 Baths
Welcome to a rare opportunity in sought-after Mariners Point! One of the largest residences in the community, this spacious 3-bedroom, 2.5-bath townhome offers an exceptional combination of generous living space, thoughtful updates, and an expansive backyard nestled against a private, tree-lined setting. Step inside to a beautifully renovated kitchen featuring all-new appliances and brand-new flooring, giving the home a fresh, updated feel that’s truly move-in ready. A cozy fireplace brings warmth and character to the main living area, while a staircase leads to an airy upper-level loft overlooking the space below. Upstairs, the spacious owner’s suite is enhanced by high ceilings, creating an open and inviting retreat. Outdoor living is equally appealing, with a sizable backyard, patio, and deck overlooking mature trees—an ideal setting for entertaining, outdoor dining, or simply relaxing in peaceful surroundings. Two driveway parking spaces add everyday convenience. Mariners Point offers a welcoming community atmosphere with a neighborhood pool and clubhouse just a short walk away, almost next door. As an added benefit, the HOA includes exterior painting every five years, helping to keep the home beautifully maintained with less exterior upkeep for the homeowner. The location is hard to beat—just minutes from Downtown Annapolis and convenient to shopping, dining, public transportation, and major commuter routes, including Forest Drive and Route 665. Everyday essentials are close at hand, with nearby shopping center and services within easy reach. Outdoor enthusiasts will love being just blocks from beautiful Quiet Waters Park, with its scenic trails, waterfront views, recreational amenities, and abundant green space. And for those drawn to the water, Chesapeake Harbour and nearby waterfront destinations are just minutes away. With its spacious floor plan, beautifully updated interior, generous outdoor space, and convenient Annapolis location, this exceptional Mariners Point home offers a rare opportunity to enjoy comfort, convenience, and the best of the Annapolis lifestyle.

908 Windwhisper Ln, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

303 Wood Hollow Ct, Annapolis
$360,000
3 Beds ⋅ 2 Baths
Discover the charm of this townhouse in the serene Whispering Woods community. This is a great opportunity to own a beautiful townhouse in Annapolis! It offers a perfect blend of comfort and functionality, making it an ideal retreat for modern living. Step inside to find a spacious layout featuring 3 inviting bedrooms, updated full bath and 1/2 bath in the basement. Enjoy a spacious updated eat in kitchen with crown molding and plenty of room to cook, gather and dine! Crown molding throughout the large living room/dining room combo. The fully finished basement, complete with a walkout entrance, provides additional living space, ideal for a home office, playroom, or cozy den. Brand new roof and attic insulation! Conveniently located near Route 50, charming downtown Annapolis with water views, shopping and dining. Don't miss the opportunity to make this charming residence your own!

303 Wood Hollow Ct, Annapolis

Listing courtesy of Maryland Residential Management Co. Contact:

1961 Marconi Cir, Annapolis
$475,000
2 Beds ⋅ 2 Baths
Welcome to 1961 Marconi Circle, located in the highly sought-after Heritage Harbour 55+ community in Annapolis! This charming 2-bedroom, 2-full-bath townhouse offers comfortable, convenient, single-level living. Step inside to a bright and inviting living room featuring beautiful flooring, coastal-inspired colors, and an abundance of natural light. The adjoining dining area flows into the kitchen, complete with white cabinetry, granite countertops, a stylish tile backsplash, and a cozy breakfast nook. The spacious primary bedroom features a private full bathroom with a walk-in shower, while the second bedroom offers flexibility for guests or a home office. Step outside to enjoy your private rear patio and fenced backyard, perfect for morning coffee, relaxing, or entertaining. Additional features include an attached one-car garage and convenient laundry area. Heritage Harbour is known for its exceptional active adult lifestyle, offering a variety of recreational amenities, clubs, and social activities. Conveniently located near downtown Annapolis, shopping, dining, and major commuter routes, this home offers the perfect opportunity to enjoy low-maintenance living in a vibrant 55+ community. Don't miss your chance to make 1961 Marconi Circle your new home!

1961 Marconi Cir, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

20 Amberstone Ct Unit H, Annapolis
$299,900
3 Beds ⋅ 2 Baths
Mid-Level Condo Available Now in the Sought After Annapolis Overlook Community. This 3 Bedroom 2 Full Bath Condo offers an Open Living Space and Balcony showing a Beautiful Wooded Backdrop to give a sense of Privacy. Features of this Home include Brand New LVP Flooring, Brand New Carpet in Bedrooms, Brand New Renovated Hall Bathroom, Freshly Painted, Stainless Steel Appliances in the Kitchen, Wood Burning Fireplace, and So Much More!!! The Annapolis Overlook Community offers a Community Center, Fitness Center, In-ground Pool, and More. Located Minutes from Downtown Annapolis.

20 Amberstone Ct Unit H, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

1952 Forest Dr, Annapolis
$435,000
3 Beds ⋅ 2 Baths
Beautiful Move-In Ready Home with Spacious Fenced Backyard! Welcome to this clean, beautiful, and well-maintained 3-bedroom, 2-full-bath home, offering comfortable living spaces and everything you need to move right in and enjoy. The inviting kitchen features beautiful granite countertops and plenty of space for cooking and entertaining. The spacious family room is highlighted by a warm, attractive fireplace, creating the perfect setting for relaxing with family and friends. Step outside and discover the large, fully fenced backyard, offering plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying your own private outdoor space. With its desirable layout, attractive finishes, spacious backyard, and move-in-ready condition, this home is a wonderful opportunity for anyone looking for comfort, convenience, and a place to call home. All information must confirm by the buyer. Don’t miss the opportunity to see this beautiful home! Schedule your showing today.

1952 Forest Dr, Annapolis

Listing courtesy of Blufin Realty, LLC.. Contact:

1503 Lodge Pole Ct, Annapolis
$350,000
3 Beds ⋅ 2 Baths
Rarely available end-unit townhome in sought-after Whispering Woods! Brand New 50 yr architectural roof! This move-in ready 3 bedroom, 1.5 bath home offers privacy and charm surrounded by mature trees. Enjoy spacious living areas, and a fenced rear yard perfect for relaxing or entertaining. Private shed provides additional storage. Conveniently located near shopping, restaurants, parks, and major commuter routes with easy access to Downtown Annapolis, Route 50, and I-97.

1503 Lodge Pole Ct, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

208 Admiral Dr, Annapolis
$325,000
2 Beds ⋅ 1 Baths

208 Admiral Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

1630 Revell Downs Dr, Annapolis
$299,000
1 Beds ⋅ 1 Baths
Welcome to 1630 Revell Downs Drive in the desirable Revell Downs community! This charming 1-bedroom, 1-bath home offers approximately 848 sq. ft. with spacious rooms, new carpeting, and an inviting living room with fireplace. The large upstairs attic offers potential for additional living space, subject to applicable approvals. Outside, enjoy a private, fully fenced rear yard with plenty of room for entertaining, gardening, or relaxing, along with an attached storage closet for added convenience. Ideally located in a quiet neighborhood just off Route 50, this home provides an easy commute while keeping you close to the Chesapeake Bay, recreation, shopping, and dining. Bay Head Park is within walking distance, and Sandy Point Beach, downtown Annapolis, and Cape St. Claire are just minutes away. Whether you're looking for a home to personalize and expand or an investment opportunity, 1630 Revell Downs Drive offers flexibility and a convenient location.

1630 Revell Downs Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

907 Windwhisper Ln, Annapolis
$420,000
2 Beds ⋅ 2 Baths
Vaulted ceilings, gleaming hardwoods, and a fireplace living room near Quiet Waters Park! Picture coming home to this updated 2-bedroom, 2-bath townhome, where country cottage charm meets move-in-ready condition. Blue-gray siding, a soaring arched window, and a gated side yard give it a storybook look from the street. The quiet Annapolis setting makes every arrival feel like a small retreat. Some images may reflect virtual staging or digital editing, including removal of personal property, to help showcase the home. The living room is the heart of the home. Vaulted ceilings rise overhead, and tall windows on either side of the fireplace pour sunlight across the hardwood floors. On cool evenings, the fireplace makes this an inviting place to unwind. A wood staircase leads to an open loft that overlooks the living area. Built-in shelving there makes it a natural fit for a reading nook, home office, or creative space. The kitchen pairs warm wood cabinetry with a built-in wine rack, modern appliances, and tile flooring. A window above the sink frames a view of the greenery outside. A sunny corner with its own window offers space for a small table or casual breakfast seating. Your primary bedroom feels just as open as the living room. It has a vaulted ceiling, crown molding, a ceiling fan, and a striking arched window that fills the room with afternoon light. The hardwood floors and inlaid border continue here, tying the home together with a polished, consistent finish. The big-ticket items are already taken care of. The HVAC system was replaced in 2024, and a new roof went on in June 2026. Your HOA fee also covers exterior painting every five years, so the townhome stays fresh on the outside with no extra effort from you. Out back, the deep yard backs up to mature trees, giving it a peaceful, wooded feel. A storage shed holds your garden tools and seasonal gear, and an assigned parking space keeps your daily routine simple. You're just off Georgetown Road, minutes from Forest Drive and Bay Ridge Road. The shopping center is close by for groceries and errands. Quiet Waters Park, Fusco Athletic Park, and Mariners Point Community Center put trails, fields, and open space within easy reach. When you're craving a view of the water, Chesapeake Harbour and Beacon Waterfront are a short drive away. A home this well-kept, with this much character, won't stay available for long. Contact us to arrange your showing and see it for yourself.

907 Windwhisper Ln, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

801 Midship Ct, Annapolis
$500,000
2 Beds ⋅ 2 Baths
Welcome to 801 Midship Court, a refreshed end unit townhouse offering 1,514 square feet of comfortable single level living in the established 55 plus community of Heritage Harbour. With two bedrooms, two full bathrooms, a flexible den, and a one car garage, the home provides an easy and practical layout. Fresh paint, new carpet, and hardwood flooring throughout the main living areas create a clean and inviting interior. The end unit setting brings additional natural light into the home, giving the living and dining spaces a bright, open feel. The primary suite includes a private bathroom, while the second bedroom is conveniently located near the hallway bathroom. Toward the rear of the home, the den provides valuable flexibility as a home office, reading room, media space, or comfortable area for guests. From here, doors open directly to the rear deck, creating a natural connection between the indoor and outdoor living spaces. A front patio offers another welcoming place to sit outside, while the rear deck provides space for relaxing or dining outdoors. The updated HVAC system and attached one car garage add comfort and convenience. Heritage Harbour offers an active community lifestyle with indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, a community Lodge, and a wide variety of clubs and activities. Shopping, dining, healthcare, and Historic Downtown Annapolis are nearby, with convenient access to Routes 50 and 97. With fresh finishes, flexible living space, two outdoor areas, and the added natural light of an end unit, 801 Midship Court is ready to welcome its next owner.

801 Midship Ct, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact:

940 Astern Way Unit 304, Annapolis
$484,900
2 Beds ⋅ 2 Baths
BACK ON THE MARKET — YOUR SECOND CHANCE IS HERE! If you were disappointed when you missed this home the first time around, you’re in luck! The current owners’ plans have changed due to a relocation, and this beautiful home is once again available. This is a rare opportunity to own a completely renovated, fully furnished home where everything is included. Just bring your personal belongings and start enjoying it! From the moment you enter, you’ll appreciate the attention to detail and the incredible transformation. This third-floor residence offers elevator access and has been renovated with a fresh, stylish look throughout. The open and inviting layout features beautiful luxury vinyl plank flooring, updated lighting, fresh paint, renovated bathrooms, and a gorgeous kitchen with white cabinetry, quartz countertops, and stainless-steel appliances. The kitchen opens to the dining area and creates a wonderful gathering space for family and friends. The comfortable living room leads into the sunroom, a perfect spot to enjoy your morning coffee, read a book, or simply take in the peaceful wooded views. Those beautiful views continue from the bedrooms, adding to the home's sense of privacy and tranquility. The primary bedroom is a true retreat with updated flooring and a beautifully renovated bath featuring dual vanities, quartz countertops, stylish lighting, ceramic tile, and a large walk-in shower. Two walk-in closets provide plenty of storage, with one thoughtfully designed as a convenient home office. The second bedroom is spacious and inviting, while the nearby full bath has also been completely updated with a new vanity, quartz countertop, modern fixtures, lighting, and tile flooring. Think of this as your opportunity to own the model home without having to furnish or decorate it yourself. The current owners have created a home that is polished, comfortable, and ready to enjoy — and they are leaving it all behind for the next owner. Enjoy an incredible community lifestyle with indoor and outdoor pools, recreation facilities, fitness center, tennis courts, walking and jogging paths, and access for kayaking and canoeing. Golf is available for an additional fee, and community transportation makes getting around even easier. Missed it the first time? Consider yourself lucky — it’s back! Beautifully renovated, fully furnished, exceptionally maintained, and ready for its next owner to move in, enjoy, and cherish. Everything is included!

940 Astern Way Unit 304, Annapolis

Listing courtesy of Academy Realty Inc.. Contact:

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